Melanogenesis inhibitory activities of iridoid-, hemiterpene-, and fatty acid-glycosides from the fruits of Morinda citrifolia (Noni)

J Oleo Sci. 2010;59(1):49-57. doi: 10.5650/jos.59.49.

Abstract

A new iridoid glycoside, 9-epi-6alpha-methoxy geniposidic acid (4), three new hemiterpene glycosides, 3-methylbut-3-enyl 2'-O-(beta-D-glucopyranosyl)-beta-D-glucopyranoside (nonioside K) (6), 3-methylbut-3-enyl 6'-O-(beta-D-xylopyranosyl)-beta-D-glucopyranoside (nonioside L) (8), and 3-methylbut-3-enyl 6'-O-(beta-D-xylofuranosyl)-beta-D-glucopyranoside (nonioside M) (9), and two new saccharide fatty acid esters, 6'-O-(beta-D-glucopyranosyl)-1'-O-[(2xi)-2-methylbutanoyl]-beta-D-glucopyranose (nonioside N) (16) and 6'-O-(beta-D-xylopyranosyl)-1'-O-[(2xi)-2-methylbutanoyl]-beta-D-glucopyranose (nonioside O) (17), were isolated from a methanol extract of the fruits of Morinda citrifolia (noni), along with 11 known compounds, namely, three iridoid glycosides (1-3), two hemiterpene glycosides (5 and 7), and five saccharide fatty acid esters (10-15). Upon evaluation of compounds 1-17 on the melanogenesis in the B16 melanoma cells induced with alpha-melanocyte-stimulating hormone (alpha-MSH), 13 compounds (1, 3, 4, 6-14, and 17) exhibited marked inhibitory effects with 34-49% reduction of melanin content at 100 muM with no or almost no toxicity to the cells (91-116% of cell viability at 100 microM).

MeSH terms

  • Antineoplastic Agents* / chemistry
  • Antineoplastic Agents* / pharmacology
  • Cell Line, Tumor
  • Fatty Acids / chemistry*
  • Fatty Acids / pharmacology
  • Fruit / chemistry*
  • Glycosides / chemistry*
  • Glycosides / pharmacology
  • Humans
  • Iridoids / chemistry*
  • Iridoids / pharmacology
  • Melanins / antagonists & inhibitors*
  • Molecular Structure
  • Morinda / chemistry*
  • Phytotherapy
  • Pigmentation / drug effects
  • Plant Preparations
  • Terpenes / chemistry*
  • Terpenes / pharmacology

Substances

  • Antineoplastic Agents
  • Fatty Acids
  • Glycosides
  • Iridoids
  • Melanins
  • Plant Preparations
  • Terpenes